Dimethylformamide → 5-Bromo-2-(3-fluorophenoxy)pyridine

HRID 77988ノート

反応式

HRID 77988 の反応式
CN(C)C=O.[F:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[H-].[Na+].Br[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1>O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)=[N:18][CH:19]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 97433-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

生成物 1

HCID 592552205-Bromo-2-(3-fluorophenoxy)pyridine収率 110.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To an N,N-dimethylformamide (100 mL) solution of 3-fluorophenol (3.30 g, 29.4 mmol) was added sodium hydride (1.41 g, 29.4 mmol, 50% in oil), which was stirred for 10 minutes at 0° C. 2,5-Dibromopyridine (4.64 g, 19.6 mmol) was then added to this mixture at 0° C., followed by 7 hours and 45 minutes of stirring at 110° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (5.81 g, quant.).

後処理

  1. waitfollowed by 7 hours and 45 minutes
  2. stirringof stirring at 110° C
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-a018755c622e43ca8214798b9a8647c1
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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